Agile Fails When Context Is Ignored

1. One-Size-Fits-All Frameworks Don’t Work

Many organizations attempt to apply Agile frameworks without considering whether they fit their specific needs. For example:

  • A small startup using SAFe just because an executive heard it works at enterprise scale.
  • A large enterprise team trying to run Scrum exactly as a five-person startup would.
  • A Kanban workflow being forced into a team that has unpredictable, research-heavy work.

While Agile frameworks provide structure, forcing a team into a specific methodology without considering their work, culture, and constraints leads to frustration and failure.

2. Agile Success Is Not Measured by Process Adoption

A team can hold daily standups, complete sprints, and update Jira boards while still being dysfunctional and ineffective. Agile is about outcomes, not rituals.

Signs of a process-driven, checklist approach to Agile:

  • Standups are status updates rather than opportunities for collaboration.
  • Retrospectives happen, but nothing changes afterward.
  • Story points and velocity are used for micromanagement rather than team improvement.

The true measure of Agile success is whether teams deliver value consistently, adapt to change, and continuously improve their ways of working.

3. Context Drives Decision-Making in Agile Coaching

An Agile coach’s role is not to enforce rules but to help teams discover what works for them. This requires a deep understanding of their specific challenges, constraints, and goals.

For example:

  • A new team may need structure and guidance, while a mature Agile team benefits more from coaching on leadership and autonomy.
  • A product-focused team may thrive with Scrum, but an infrastructure team might be better suited to Kanban.
  • An enterprise Agile transformation requires alignment across departments, while a startup can pivot quickly without heavy processes.

By coaching with context in mind, teams are empowered to make Agile their own rather than follow it as a set of rules.


How Agile Coaches Can Adapt to Context

1. Start with Discovery, Not Solutions

Instead of prescribing a framework upfront, begin with observation and inquiry.

  • How does the team currently work?
  • What are their biggest challenges?
  • What constraints (organizational, technical, cultural) affect them?

Understanding the team’s existing dynamics and pain points leads to more meaningful coaching.

2. Focus on Outcomes, Not Just Practices

Instead of asking, “Are you following Agile best practices?”, ask:

  • Are we delivering value consistently?
  • Are teams collaborating effectively?
  • Is there psychological safety for learning and improvement?

Agile processes should evolve based on what helps teams improve, not just what is written in a playbook.

3. Help Teams Own Their Agile Journey

Coaches should guide teams to experiment and reflect rather than dictate how Agile should be done. Encourage:

  • Retrospectives with real impact—where teams commit to actionable change.
  • Flexibility in frameworks—mixing elements of Scrum, Kanban, and Lean based on their needs.
  • Decentralized decision-making—so teams shape their own Agile practices instead of waiting for top-down mandates.

When teams take ownership of their ways of working, Agile is no longer a checklist—it becomes an evolving practice of continuous improvement.


Final Thoughts: Agile as a Living System

Agile coaching should not be about enforcing compliance to a framework. It should be about helping teams build an adaptable, sustainable way of working that aligns with their goals and challenges.

Instead of asking, “Is the team following Agile?”, ask:

  • Are they delivering value?
  • Are they improving over time?
  • Are they engaged and motivated?

The best Agile coaches don’t just teach Agile—they help teams shape it for themselves.

What’s Next?

How do you approach Agile coaching in different team contexts? Have you seen teams struggle by applying Agile rigidly? Let’s discuss—drop a comment or connect with me.

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